Skip to main content
SpringerLink
Log in

Inhibitory effect of anethole in nonimmune acute inflammation

  • Original Article
  • Published:
Naunyn-Schmiedeberg's Archives of Pharmacology Aims and scope Submit manuscript

Abstract

Anethole [1-methoxy-4-(1-propenyl)benzene] occurs naturally as a major component of the essential oil of star anise (Illicium verum Hook.f., family Illiciaceae), comprising more than 90 % of its volatile components. Studies showed that this substance has antioxidant, antibacterial, antifungal, and anesthetic properties. In this study, the anti-inflammatory properties of anethole in animal models of nonimmune acute inflammation such as croton oil-induced ear edema and carrageenan-induced pleurisy were investigated. The investigated parameters were edema formation, leukocyte migration, and inflammatory mediators involved. Oral administration of anethole at a dose of 250 and 500 mg/kg reduced both the volume of pleural exudates and the number of migrated leukocytes. Levels of nitric oxide (NO) and prostaglandins (PGE2) in the inflammatory exudate were reduced by treatment with anethole, but levels of tumor necrosis factor-α and interleukin-1β were not significantly altered. In ear edema, the oral treatment with anethole inhibited the formation of exudate and the activity of myeloperoxidase, but not after topical administration. These results suggest that the anethole may be effective in controlling some nonimmune acute inflammation-related disease, probably by an inhibitory action on production and/or release of PGE2 and NO.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  • Adams RP (2007) Identification of essential oil components by gas chromatography/mass spectroscopy, 4th edn. Allured Publishing Corporation, Carol Stream

    Google Scholar 

  • Bradley PP, Priebat DA, Chiristensen RD, Rothstein G (1982) Mesurement of cutaneous inflammation: estimation of neutrophil content with an enzyme marker. J Inv Dermatol 78:206–209

    Article  CAS  Google Scholar 

  • Chainy GBN, Manna SK, Chaturvedi MM, Aggarwal BB (2000) Anethole blocks both early and late cellular responses transduced by tumor necrosis factor: effect on NF-kB, AP-1, JNK, MAPKK and apoptosis. Oncogene 19:2943–2950

    Article  CAS  PubMed  Google Scholar 

  • Chantraine JM, Laurent D, Ballivian C, Saavedra G, Ibañez R, Vilaseca LA (1998) Insecticidal activity of essential oils on Aedes aegypti larvae. Phytother Res 12:350–354

    Article  CAS  Google Scholar 

  • Formulário de Fitoterápicos da Farmacopéia Brasileira (2011) Agência Nacional de Vigilância Sanitária ANVISA Brasília, Brazil

  • Dzamic A, Sokovic M, Ristic MS, Grijic-Jovanovic S, Vukojevic J, Marin PD (2009) Chemical composition and antifungal activity of Illicium verum and Eugenia caryophyllata essential oils. Chem Nat Comp 45:259–261

    Article  CAS  Google Scholar 

  • Estevão-Silva CF (2012) Efeito dos constituintes de óleos essenciais (anetol e eugenol) sobre a migração de leucócitos in vitro e in vivo. Dissertation, State University of Maringá-PR, Brazil

  • Faurschou M, Borregaard N (2003) Neutrophil granules and secretory vesicles in inflammation. Microbes Infect 2:364–371

    Google Scholar 

  • Freire RS, Morais SM, Catunda-Junior FEA, Pinheiro DCSN (2005) Synthesis and antioxidant, anti-inflammatory and gastroprotector activities of anethole and related compounds. Bioorg Med Chem 13:4353–4358

    Article  CAS  PubMed  Google Scholar 

  • Geroniakaki AA, Gavalas A (2006) Antioxidants and inflammatory disease: synthetic and natural antioxidants with anti-inflammatory activity. Comb Chem High Throughput Screen 9:425–442

    Article  Google Scholar 

  • Gilroy DW, Colville-Nash PR, Willis D, Chivers J, Paul-Clark MJ, Willoughby DA (1999) Inducible cyclooxygenase may have anti-inflammatory properties. Nat Med 5:698–701

    Article  CAS  PubMed  Google Scholar 

  • Goodman R, Mantegna LR, Mcallister CL, Bruin E, Dowling RL, George H, Feeser W, Freimark B, Lischwe M, Pick S, Harris RR, Kerr JS (1993) IL-1 and its role in rat carrageenan pleurisy. Mediators Inflamm 2:33–39

    Article  CAS  PubMed  Google Scholar 

  • Grisham MB, Johnson GG, Lancaster JR (1996) Quantification of nitrate and nitrite in extracellular fluids. Methods Enzymol 268:237–246

    Article  CAS  PubMed  Google Scholar 

  • Harada Y, Hatanaka K, Kawamura M, Saito M, Ogino M, Majima M, Ohno T, Ogino K, Yamamoto K, Taketani Y, Yamamoto S, Katori M (1996) Role of prostaglandin H synthase-2 in prostaglandin E2 formation in carrageenin-induced pleurisy. Prostaglandins 5:19–23

    Google Scholar 

  • Iwata M, Suzuki S, Asai Y, Inoue T, Takagi K (2010) Involvement of nitric oxide in rat model of carrageenan-induced pleurisy. Mediators Inflamm 2010:1–11

    Article  Google Scholar 

  • Kosalec I, Peljnjak S, Kustrak D (2005) Antifungal activity of fluid extract and essential oil from anise fruits (Pimpinella anisum L., Apiaceae). Acta Pharm 55:377–385

    CAS  PubMed  Google Scholar 

  • Lemos HO, Grespan R, Vieira SM, Cunha TM, Verri-Junior WA, Fernandes KSS, Souto FO, McInnes IB, Ferreria SH, Liew FY, Cunha FG (2009) Prostaglandin mediates IL-23/IL-17-induced neutrophil migration in inflammation by inhibiting IL-12 and IFN production. Proc Natl Acad Sci USA 106:5954–5959

    Article  CAS  PubMed  Google Scholar 

  • Lima RK, Cardoso MG, Moraes JC, Vieira SS, Melo BA, Filgueiras CC (2008) Composição dos Óleos Essenciais de Anis-estrelado Illicium verum L. e de Capim-limão Cymbopogon citratus (DC.) Stapf: Avaliação do Efeito Repelente sobre Brevicoryne brassicae (L.) (Hemiptera: Aphididae). BioAssay 3:1–6

    Google Scholar 

  • Moore AR (2003) Pleural models of inflammation: immune and nonimmune. Methods Mol Biol 118:123–128

    Google Scholar 

  • O’Dell JR (2004) Therapeutic strategies for rheumatoid arthritis. New Eng J Med 350:2591–2602

    Article  PubMed  Google Scholar 

  • Otuki MF, Vieira-Lima F, Malheiros A, Yunes RA, Calixto JB (2005) Topical anti-inflammatory effects of the ether extract from Protium kleinii and α-amyrin pentacyclic triterpene. Eur J Pharmacol 507:253–259

    Article  CAS  PubMed  Google Scholar 

  • Paula-Neto HA, Alves-Filho JC, Souto FO, Spiller F, Amêndoa RS, Freitas A, Cunha FQ, Barja-Fidalgo C (2011) Inhibition of guanylyl cyclase restores neutrophil migration and maintains bactericidal activity increasing survival in sepsis. Shock 35:17–27

    Article  CAS  PubMed  Google Scholar 

  • Paul-Clark MJ, Gilroy DW, Willis D, Willoughby DA, Tomlinson A (2001) Nitric oxide synthase inhibitors have opposite effects on acute inflammation depending in their route of administration. J Immunol 166:1169–1177

    CAS  PubMed  Google Scholar 

  • Payan DG (1989) Neuropeptides and inflammation: the role of substance P. Annu Rev Med 40:341–352

    Article  CAS  PubMed  Google Scholar 

  • Ponte EL, Sousa PL, Rocha MVAP, Soares PMG, Coelho-de-Souza AN, Leal-Cardoso JH, Assreuy AMS (2012) Comparative study of anti-edematogenic effects of anethole and estragole. Pharmacol Rep 64:984–990

    CAS  PubMed  Google Scholar 

  • Ritter AMV, Domiciano TP, Verri-Junior WA, Zarpelon AC, Silva LG, Barbosa CP, Natali MRM, Cuman RKN, Bersani-Amado CA (2012) Antihypernociceptive activity of anethole in experimental inflammatory pain. Inflamopharmacology. doi:10.1007/s10787-012-0152-6

  • Saleh TSF, Calixto JB, Medeiros YS (1997) Proinflammatory effects induced by bradykinin in a murine model of pleurisy. Eur J Pharmacol 331:43–52

    Article  CAS  PubMed  Google Scholar 

  • Schulz V (2002) Fitoterapia Racional. Um guia de fitoterapia para as Ciências da Saúde. Manole, São Paulo

    Google Scholar 

  • Tomlinson A, Appleton I, Moore AR, Gilroy DW, Willis D, Mitchell JA, Willoughby DA (1994) Cyclo-oxygenase and nitric oxide synthase isoforms in rat carrageenin-induced pleurisy. British J Pharmacol 113:693–698

    Article  CAS  Google Scholar 

  • Verri WA Jr, Souto FO, Vieira SM, Almeida SC, Fukada SY, Xu D, Alves-Filho JC, Cunha TM, Guerrero AT, Mattos-Guimaraes RB, Oliveira FR, Teixeira MM, Silva JS, McInnes IB, Ferreira SH, Louzada-Junior P, Liew FY, Cunha FQ (2010) IL-33 induces neutrophil migration in rheumatoid arthritis and is a target of anti-TNF therapy. Ann Rheum Dis 9:1697–1703

    Google Scholar 

  • Vinegar R, Truax JF, Selph JL (1973) Some quantitative temporal characteristics of carrageenin-induced pleurisy in the rat (37397). Proc Soc Exp Biol Med 143:711–714

    CAS  PubMed  Google Scholar 

  • Wang GW, Hu WT, Huang BK, Qin LP (2011) Illicium verum: a review on its botany, traditional use, chemistry and pharmacology. J Ethnopharmacol 136:10–20

    Article  CAS  PubMed  Google Scholar 

  • Yea SS, Jeong HS, Choi CY, Park KR, Oh S, Shin JG, Yun CH (2006) Inhibitory effects of anethole on T-lymphocyte proliferation and interleukin-2 production through down-regulation on the NK-AT and AP-1. Toxicol In vitro 20:1098–1105

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgments

We gratefully acknowledge the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior, the Conselho Nacional de Desenvolvimento Científico e Tecnológico, and the Fundação Araucária for the financial support.

Author information

Authors and Affiliations

  1. Laboratory of Inflammation, Department of Pharmacology and Therapeutic, State University of Maringá, Maringá, Paraná, Brazil

    Talita Perdigão Domiciano, Alessandra Mileni Versuti Ritter, Camila Fernanda Estevão-Silva, Fernando Seara Ramos, Silvana Martins Caparroz-Assef, Roberto Kenji Nakamura Cuman & Ciomar Aparecida Bersani-Amado

  2. Laboratory of Immunology, Department of Health Basic Science, State University of Maringá, Maringá, Paraná, Brazil

    Márcia Machado de Oliveira Dalalio

  3. Department of Chemistry, State University of Maringá, Maringá, Paraná, Brazil

    Expedito Leite Silva

Authors
  1. Talita Perdigão Domiciano
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Márcia Machado de Oliveira Dalalio
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Expedito Leite Silva
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Alessandra Mileni Versuti Ritter
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Camila Fernanda Estevão-Silva
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Fernando Seara Ramos
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Silvana Martins Caparroz-Assef
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Roberto Kenji Nakamura Cuman
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Ciomar Aparecida Bersani-Amado
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ciomar Aparecida Bersani-Amado.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Domiciano, T.P., Dalalio, M.M.O., Silva, E.L. et al. Inhibitory effect of anethole in nonimmune acute inflammation. Naunyn-Schmiedeberg's Arch Pharmacol 386, 331–338 (2013). https://doi.org/10.1007/s00210-012-0820-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00210-012-0820-5

Keywords

Search

Navigation